Skip to Content
Merck
CN
All Photos(1)

Documents

14606

Sigma-Aldrich

Cholesterol

tested according to Ph. Eur.

Sign Into View Organizational & Contract Pricing
All Photos(1)
Synonym(s):
Cholesterolum, 3β-Hydroxy-5-cholestene, 5-Cholesten-3β-ol
Empirical Formula (Hill Notation):
C27H46O
CAS Number:
57-88-5
Molecular Weight:
386.65
Beilstein:
1915888
EC Number:
200-353-2
MDL number:
MFCD00003646
UNSPSC Code:
41141804
PubChem Substance ID:
329750548
NACRES:
NA.21

Agency

USP/NF
tested according to Ph. Eur.

Quality Level

100

form

powder

bp

360 °C (lit.)

mp

147-149 °C (lit.)

solubility

chloroform: soluble 1 gm in 4.5 ml
diethyl ether: soluble 1 gm in 2.8 ml
pyridine: soluble 1 gm in 1.5 ml
H2O: insoluble
acetone: soluble
alcohol: slightly soluble
alcohol: very soluble (Hot)
benzene: soluble
dioxane: soluble
ethyl acetate: soluble
hexane: soluble
oil: soluble
petroleum ether: soluble

density

1.067 g/mL at 25 °C (lit.)

application(s)

pharmaceutical (small molecule)

storage temp.

2-8°C

SMILES string

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI key

HVYWMOMLDIMFJA-DPAQBDIFSA-N

Gene Information

human ... POLA1(5422) , TOP2A(7153)
rat ... Ar(24208) , Polb(29240)

Looking for similar products? Visit Product Comparison Guide

Application

Cholesterol was used for preparing ISCOMS containing ovalbumin (OVA) for studying whether the incorporation of the protein antigen ovalbumin (OVA) in lipophilic immune-stimulating complexes (ISCOMS) induces very strong primary immune responses. It was incorporated in animal feed to study the effect of cholesterol-rich diet.

Biochem/physiol Actions

Cholesterol is a lipid that makes up about 20-25% of the structural components of the cell membranes. It determines the fluidity and permeability of the membrane, making it permeable to water but not to ions and protons. Cholesterol also regulates the functions of the transporters and signaling proteins present on the plasma membrane. The major sites of cholesterol synthesis are small intestine and liver.
Major component of all biological membranes; ~25% of total brain lipid is cholesterol.

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Ricardo L F Guerra et al.
Lipids in health and disease, 6, 16-16 (2007-07-04)
Exercise has been prescribed in the treatment and control of dyslipidemias and cholesterolemia, however, lipid responses to different training frequencies in hypercholesterolemic men have been inconsistent. We sought to verify if different frequencies of continuous moderate exercise (2 or 5
Daniela C U Cavallini et al.
Lipids in health and disease, 8, 1-1 (2009-01-09)
Much attention has been drawn to different alternative strategies for cardiovascular disease prevention. The aim of the present study was to observe and compare the effects of Enterococcus faecium CRL183 (probiotic microorganism), an isoflavones mixture and simvastatin (drug used to
John M Dietschy et al.
Journal of lipid research, 45(8), 1375-1397 (2004-07-16)
Unesterified cholesterol is an essential structural component of the plasma membrane of every cell. During evolution, this membrane came to play an additional, highly specialized role in the central nervous system (CNS) as the major architectural component of compact myelin.
R R Grummer et al.
Journal of animal science, 66(12), 3160-3173 (1988-12-01)
Cholesterol utilized for steroid synthesis by ovarian tissue may be derived from de novo synthesis or cellular uptake of lipoprotein cholesterol. The majority of blood cholesterol is transported by either low (LDL) or high (HDL) density lipoproteins, depending on the
Matthew P Buman et al.
American journal of epidemiology, 179(3), 323-334 (2013-12-10)
Sleep and sedentary and active behaviors are linked to cardiovascular disease risk biomarkers, and across a 24-hour day, increasing time in 1 behavior requires decreasing time in another. We explored associations of reallocating time to sleep, sedentary behavior, or active
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service